EFFICIENT ONE-POT SYNTHESIS OF SUBSTITUTED OXAZOLES FROM 3-TRIMETHYLSILYLPROPARGYLIC ALCOHOLS AND AMIDES BY GOLD-CATALYZED SUBSTITUTION FOLLOWED BY CYCLOISOMERIZATION

被引:7
|
作者
Morita, Nobuyoshi [1 ]
Sano, Aoi [1 ]
Sone, Ayako [1 ]
Aonuma, Shino [1 ]
Matsunaga, Arisa [1 ]
Hashimoto, Yoshimitsu [1 ]
Tamura, Osamu [1 ]
机构
[1] Showa Pharmaceut Univ, Machida, Tokyo 1948543, Japan
关键词
PROPARGYLIC ALCOHOLS; GOLD(I)/(III)-CATALYZED SYNTHESIS; FUNCTIONALIZED OXAZOLES; MEDIATED SYNTHESIS; CYCLIZATION; SEQUENCE;
D O I
10.3987/COM-18-S(T)81
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Trimethylsilylpropargylic alcohols 1, on treatment with amides 2 in the presence of catalytic amounts of cationic gold(III), underwent propargylic substitution followed by cycloisomerization, in which the key feature is the beta-cation-stabilizing effect of the silicon atom of 1.
引用
收藏
页码:719 / 728
页数:10
相关论文
共 50 条
  • [31] One-Pot Synthesis of Pentasubstituted Pyrroles from Propargylic Alcohols, Amines, and Dialkyl Acetylenedicarboxylates; Tandem Amination, Propargylation and Cycloisomerization Catalyzed by Molecular Iodine
    Bhunia, Nisith
    Das, Biswanath
    SYNTHESIS-STUTTGART, 2013, 45 (08): : 1045 - 1050
  • [32] Silica Chloride-Catalyzed Microwave-Assisted Efficient and Selective One-Pot Synthesis of Amides from Aldehydes
    Datta, Bandita
    Pasha, M. A.
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (07): : 2129 - 2130
  • [33] One-Pot Synthesis of N-Substituted β-Amino Alcohols from Aldehydes and Isocyanides
    Cioc, Razvan C.
    van der Niet, Daan J. H.
    Janssen, Elwin
    Ruijter, Eelco
    Orru, Romano V. A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (21) : 7808 - 7813
  • [34] One-pot synthesis of α-iodo-substituted α,β-unsaturated aldehydes from propargylic alcohols
    Chen, Shufeng
    Wang, Jianbo
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13): : 4993 - 4996
  • [35] Facile one-pot synthesis of three different substituted thiazoles from propargylic alcohols
    Gao, Xun
    Pan, Ying-ming
    Lin, Min
    Chen, Li
    Zhan, Zhuang-ping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (14) : 3259 - 3266
  • [36] Synthesis of 1-Arylnaphthalenes by Gold-Catalyzed One-Pot Sequential Epoxide to Carbonyl Rearrangement and Cyclization with Arylalkynes
    Gudla, Vanajakshi
    Balamurugan, Rengarajan
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (02) : 414 - 428
  • [37] An efficient one-pot protocol for the synthesis of phenyl substituted 3-silatetrahydropyrans
    Kirpichenko, Svetlana V.
    Shainyan, Bagrat A.
    TETRAHEDRON, 2015, 71 (04) : 599 - 604
  • [38] L-proline catalyzed an efficient multicomponent one-pot synthesis of poly substituted pyridines
    Janardhan, B.
    Ravibabu, V.
    Crooks, Peter. A.
    Rajitha, B.
    ORGANIC COMMUNICATIONS, 2012, 5 (04) : 186 - 195
  • [39] One-pot synthesis of substituted 2,5-dihydrofurans from β-oxo amides and cinnamaldehydes
    Liu, Xu
    Xin, Xin
    Xiang, Dexuan
    Liang, Yongjiu
    Xin, Xiaoqing
    Li, Wenliang
    Dong, Dewen
    RSC ADVANCES, 2013, 3 (05): : 1346 - 1349
  • [40] Iodine-catalyzed one-pot synthesis of amides from nitriles via Ritter reaction
    Theerthagiri, Palani
    Lalitha, Appaswami
    Arunachalam, Pirama Nayagam
    TETRAHEDRON LETTERS, 2010, 51 (21) : 2813 - 2819